


Double Trouble

by halfpastten



Series: Pokemon Smut Collection [11]
Category: Pocket Monsters | Pokemon - All Media Types
Genre: Anal Sex, Anal Virginity, Anatomically Correct Snek, Blow Jobs, Double Penetration, Enthusiastic Consent, Hemipenes, Kinda, Licking, M/M, Mistaken Gender, Plot What Plot/Porn Without Plot, Pokephilia, Rutting, Shameless Smut
Language: English
Status: Completed
Published: 2020-02-02
Updated: 2020-02-05
Packaged: 2021-02-28 06:26:28
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 4,492
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22529311
Author URL: https://archiveofourown.org/users/halfpastten/pseuds/halfpastten
Summary: Marcus has always dreamed of doing a pretty Serperior lady. So when he catches one, he can't wait to get it on with... him?Wait,what?A story of exploration, in three acts.
Relationships: Jalorda | Serperior/Original Male Character(s)
Series: Pokemon Smut Collection [11]
Series URL: https://archiveofourown.org/series/1615384
Comments: 9
Kudos: 109





	1. Chapter 1

"Oh boy, oh boy... okay, here we go."

Marcus paced in his bedroom, the Ultraball in his hands. He'd prepared the room, cleaned it up and made the bed with fresh linens. A new, unopened bottle of his favourite lube was placed prominently on the nightstand, and the Trainer himself was only wearing a pair of boxers. He hesitated, rubbing a hand over his slightly pouchy belly, lamenting his lack of shape. Still, he was hopeful that the beautiful Serperior wouldn't mind it too much, and that she'd be as interested in having sex as he was. Most Pokemon were, at least those he'd caught over the years, but today was important. "Can't believe I finally found you," he murmured towards the Ultraball where his new Serperior was resting in. He felt heat tingling in his belly and swallowed down his nerves. "You'll need a name, right? Come out, Serperior!"

A red light flashed inside the room, and there she was, just as beautiful as yesterday when he'd caught her. Her long, sensual body was coiled up as she blinked the sleep away, the very top of her tail waving a little. Red eyes focussed on the Trainer, who couldn't stop the swelling of his eager cock even if he'd bothered to try. "You look like an Evelyn," he told the Serperior, who blinked twice and smiled bashfully before slithering close. Marcus held his breath when the Pokemon reared up to face her new Trainer, nuzzling his cheek after a moment.

"So lovely," he murmured, finally daring to touch the smooth scales. He let his fingers wander over the strong body of the snake Pokemon and was delighted when Evelyn leaned into the touch.

"Serperior", she said in an oddly deep voice, fluttering long eyelashes at him. The tip of her tail brushed his hairy thighs and flicked against his half-hard cock, making him moan. How anyone could _not_ want to fuck with Pokemon, really - most of them were willing to get it on after being caught.

"Come on, beaut, let's get to know each other really good," Marcus said with a hoarse voice, leading Serperior towards his bed. She was heavy, almost three and a half meters long and all muscles, so the bed groaned when they both climbed on it. Having done his research, Marcus immediately started to greedily explore her body, massaging the long body as he pressed kisses onto her snout. Evelyn was just as eager as he, wrapping her body all around him and brushing his lips with her red tongue. When his fingers finally found the thin slit on the last third of her body, her whole body shuddered, pressing herself against his rubbing hand. Marcus grinned - she was a bit swollen there, so it was easy to push a finger into the hot slit and...

"What..."

Evelyn gave a hum, pushing against him, and something hot and oddly firm started pushing out of the slit, the texture wholly alien to him. Marcus stared down at where his hand was pressed against Evelyn's body. His finger got pushed out, and what followed was definitely no pussy. The slit opened up and gave way to a twitching _thing_ \- a white, thick shaft bulbing out in the middle where it started to turn into a reddish colour. It ended in two cockheads, the skin heavily textured like deep red cells. It rubbed against his now unmoving hand, and it felt hot and wet against his skin.

Before Marcus could even open his mouth, another of these things wiggled out the slit. Evelyn made a lewd noise, coiling tighter around the shocked Trainer. "You... are a dude?" he finally managed to ask and looked up, only to see Evelyn nodding. Marcus swallowed and was just a moment away from calling this whole thing off and placing Evelyn back in her... **his** Ultraball, but the Serperior leaned forward to nuzzle against him, pressing his two cocks firmly against Marcus' hand. A hot wave of arousal raced through his body, making his still-hard cock jolt in surprise. "Whoah..." he said, his free arm grabbing Serperior and hugging him close. His reaction surprised him, because he'd never even _thought_ about fucking with male Pokemon, but... but this was _Serperior_.

Maybe that was the reason why his cock was still leaking. He'd fantasized so often about getting it on with a Serperior that he now reacted like that to one without regards to the gender. Hesitantly he started to touch one of the cocks, feeling weird and awkward doing so. Evelyn sighed in comfort, cuddling closer as he got touched, and with another swallow, Marcus rubbed the silky-smooth shaft up and down before exploring one of the squishy heads, letting his thumb run across the textured skin there.

It caused Evelyn to moan, and _fuck_ , okay, Marcus definitely liked that. "I'll be honest," he said, voice a bit raspy and continuing to play with the one cock in his hand while rubbing his other hand along Serperior's long back. "I totally thought you're a... well, a girl. I kinda never had sex with a guy before."

He grimaced when he heard Evelyn snicker. "It's not funny, okay? I don't really know how to do this. Not that- I mean, I *still* want to do it. So, uh... Do we jerk each other off? We could rub our cocks together if you want?"

The idea sounded pretty good to himself. Evelyn's cocks were definitely freaky, but he couldn't stop touching and playing with them, and the thought of getting his cock between those textured cockheads was... yeah, that was really nice, wasn't it. Evelyn seemed to think so as well, with how fast he nodded. Still snickering, still grinning, but also agreeing with the Trainer. Marcus huffed, but pulled his boxers down all the same, exposing his throbbing cock. He was pretty proud of it - for a human, he was nice and hung, his shaft girthy and his cockhead angry red and leaking from the slit. Evelyn shifted closer, pressing his own two cocks against Marcus' crotch and the heat was almost as good as a Pokemon's pussy.

Moaning, Marcus tried to close his hand around all three shafts. He really liked the silky smooth feeling of Evelyn's white shafts, rubbing his fingers against it, but all three cocks were too much to hold onto with just one hand. That was when Evelyn rutted forward, his movable cocks sandwiching his own meaty length. The texture of the red cockheads was so new and exotic, Marcus couldn't help but thrust right into the hot embrace, spilling more precum. "Fuck," he said, gasping for air as one of the cockheads rubbed against his. "Fuck, Evelyn, this feels really good!"

Evelyn hummed, eyes fluttering close as the Serperior thrust against him. They both moved a bit clumsy, Marcus unsure how to coordinate himself correctly, but they still got enough friction going to send both of them in a frenzy. Putting his arm around the tense body of Evelyn, Marcus braced himself and slammed his hips forward, letting his cock slide between the other two, hugging Evelyn close while moaning without restraint. "Ugh... nggh, Evelyn, fuck, so good... your cocks feel so good!"

And wasn't that weird, that this was just as exciting as fucking into a pussy? But being male didn't make Evelyn any less beautiful, his body less arousing to Marcus. Nor did the feeling of two cocks throbbing and twitching against his own put him off. To be honest, it turned him on like nothing else, the knowledge that he was rubbing cocks with another male who rutted against him just as forceful as Marcus did. All the new sensations brought him fairly quickly to the edge, however, and with a last squirm, he came heavily, spurting his thick ropes of cum all over his Pokemon lover, making Evelyn hiss in delight, following up with his own orgasm. Four cockheads released their juice, covering Marcus' cock and belly with their thick fluid, leaving both messy and gasping for air in a hot tangle.

"Fuck," Marcus finally managed to say, cuddling closer to Evelyn and touching his belly, getting his fingers sticky with another male's cum. He rubbed it between his fingers before he yelped as Evelyn brought his head between their bodies, licking up both of their cum with a satisfied hum. "Shit, you like that?" Marcus stared at him, then at his cum-covered fingers, before he brought his hand to his mouth and licked tentatively. It tasted... weird. Too bitter, a tad salty, warm on his tongue. He licked again, rather sceptical, then let Evelyn clean up their cocks as both grew limp after having spent their cum.

"Thanks, Evelyn," Marcus said, then he paused. "Uhm... is the name okay? It's a girl's name, after all, and with you being not..."

Evelyn interrupted him with an amused hiss, letting his cocks pull back into the protective slit. It closed soon after. "Okay, then Evelyn it is. Suits you, you're really pretty." That earned Marcus another nuzzle. He grinned and let his confusion slip. It didn't really matter that he enjoyed it, after all. It had been fucking amazing, fooling around with his new, male Serperior, and if that made him Bi or whatever, well - plenty more holes to fuck from now on.

**Notes for the Chapter:**

> Double-cocked snake Pokemon should be canon. For anyone wondering how Evelyn's Hemipenes looks like, feel free to google that term. Warning: Contains snake genitalia.  
> Tags are for the complete story - Marcus and Evelyn will explore what they can do together over the course of this work.
> 
> **You're welcome to leave prompts and suggestions in my Idea Collection. ☺**


	2. Chapter 2

Marcus sighed, leaning back in his chair. Being a Pokemon Trainer was all well and good, but some of the paperwork was utterly ridiculous if you wanted to apply at your local Gym. Stretching out, he let his eyes wander over the row of his prized Pokemon. Most of his collection sat safely in his PC or were with the local Professor, but he'd build a shelf sitting above the headboard of his bed for his main team.

Feeling a bit horny, he contemplated which one of his favourites he should bed today. They were all eager enough, and he loved them dearly, which was why he never gave a fuck about the opinions of the public who'd state him a rapist for using his Pokemon for sex - there was no 'using' in that equation, not when he never touched those who didn't want to tangle in the sheets with him. Like his female Krookodile, who'd expressed no interest to his advances, but was loyal and great in a fight all the same.

His eyes caught onto one of the Ultraballs on the shelf and he smiled to himself. It had been a fortnight since catching his Serperior, and the two of them had quite the fun rutting against each other ever since. His cock gave an interested twitch, warming up to the idea to spend some extra time with his only male Pokemon in his collection. Making up his mind, he hesitated a bit before pulling out a bottle of lube from a drawer before grabbing the ball. He'd read up some more about the anatomy of Serperiors and was eager to act upon it. "Come out, Evelyn," he calls, throwing his ball, and soon after his dear Serperior slithered up to him, greeting him with a nuzzle as he coiled around his human. "Hmmh... hey, missed me?" Marcus greeted him and wrapped his arms around the powerful body, giving him a kiss on the tip of his snout. Evelyn's tongue darted out and met the lips, and Marcus didn't hesitate to let Evelyn explore his mouth, opening his lips as an invite.

"I was thinking about trying something else today if you don't mind. What do you think about me fucking you?", he asked and grinned when Evelyn perked up. Giving an enthusiastic nod, the Serperior let go of his Trainer and climbed the bed, not minding the creaking noises the poor frame made. Marcus came over, giving his own cock a squeeze through his trousers and eyed the beautiful Pokemon on his bed. He licked his lips and started kissing the smooth scales, rubbing his hands over Evelyn's body. He was far beyond thinking it weird to fondle a male Pokemon, although he was oddly nervous about going down on Evelyn, which he was planning to do. But the aroused hissing noises Evelyn made gave him enough motivation and his tongue and lips were soon covering Evelyn's slightly swollen slit in wet kisses. Already one of Evelyn's cocks was trying to wiggle out, not yet hard enough to get past the opening, and with a deep breath, Marcus dipped down to lick against the half-exposed cockhead, feeling the spongy surface yielding under the pressure he put against it.

Evelyn arched that part of his body, his tail coiling around Marcus' waist, the tip brushing his crotch where his hard cock was tenting out his trousers. Marcus moaned against the slit and felt Evelyn's cock sliding out and against his lips. The taste was still weird, but nothing he minded too much as he grabbed the silky smooth, white shaft and put one of the cockheads into his mouth. His sucking was a bit clumsy, only knowing how it was to _get_ a blowjob, but it was enough to make Evelyn shudder and push out his second cock, which Marcus was quick to fondle as well.

He spent some time to suck and lick on each of the cockheads, all the while rubbing and squeezing both shafts. They were trembling in his grasp. When Marcus moved between the cocks, Evelyn spread them, exposing his hole nestled between them. This section was swollen, so it didn't sit deep inside the slit, easily reachable for Marcus' tongue. Swallowing, Marcus nuzzled between the cocks, which immediately pressed against his cheeks as he licked the twitching hole. Evelyn shuddered again, a low hiss escaping him, followed by a louder one when Marcus' tongue circled the hole and prodded inside, swishing around. It was wet and warm and had the same silky smooth texture as Evelyn's shafts.

Sitting back up, Marcus grabbed the lube bottle and coated his fingers with lube before reaching down again. His index finger slid easily into the Serperior and Marcus took his time to marvel at this hot hole and the muscles clamping down greedily on his finger. Sliding a second one in, he started feeling around, pushing against the smooth walls and rubbing upwards, making Evelyn wriggle on the bed. "You like that, don't you?", he asked, voice raspy with lust, his trousers too tight and restricting his raging boner. With his free hand, he opened up his trousers and pulled them down. His cock, finally free, jumped out and smacked against his own belly, dribbling precum all over himself. "Want to feel the real deal? You'll be the first guy to get this cock, Evelyn."

Evelyn hissed in delight, wriggling again and clenching down on Marcus' fingers. He twisted them before pulling out and straddling Evelyn, pointing his cock down and at the twitching hole of the snake Pokemon. He made quick work drizzling more lube into Evelyn's hole, coating his cock as well, then he pushed his fat cockhead forward and groaned loudly when Evelyn's body enveloped him. "Fuck, Evelyn," he rasped, pushing deeper. It felt like Evelyn's hole was sucking him in, hot and smooth and wet like a prime pussy. "Fuck, you like my cock in your cunt, don't you?" He shifted slightly before laying down on top of Evelyn, thrusting his hips forward and sliding his cock home until he was balls-deep inside his Pokemon. He could feel Evelyn's cocks rubbing against his balls - he loved how dexterous they were. For a brief moment, he tried to imagine how one of them would feel up his arse - Evelyn certainly enjoyed being penetrated, panting loudly and coiling his end tail around one of Marcus' legs.

Kissing Evelyn's snout, Marcus started to fuck into him, trying to keep up a steady rhythm. The lube in Evelyn's hole created an obscene smacking noise, and soon both of them were grunting against each other as Marcus' thrusts got harder and faster until he was pistoning in and out of Evelyn with enough force to make the bed creak and groan as well, muscles flexing. His skin was coated in sweat as he continued - Evelyn was wonderfully tight, his muscles clenching around him as if to milk him dry. "Fuck, fuck, Evelyn, so good," he shouted, his balls slapping against Evelyn's cocks with the force of his thrusts. He was taking it so well, his hole feeling so perfect as if made for his cock.

Surprisingly, Evelyn came first. Marcus could feel the Serperior's cocks twitching wildly before releasing hot ropes of cum over his balls and thighs. He grunted as Evelyn's hole clamped down on him, but he managed to keep going for another solid minute before the heat was overwhelming him, sharp pleasure chasing down his spine. With a strangled cry, he buried deep into Evelyn, his cock throbbing once, twice before he shot his load, coating Evelyn's insides with his fresh cum.

They needed some time to calm down. Marcus' hands were shaking slightly when he stroke over Evelyn's scaled body, his breath ragged and heart pumping loudly in his chest. He felt himself soften and pulled his cock out of him, a string of sticky cum still connecting him to Evelyn's hole for a lingering moment. Then he rolled off of Evelyn, feeling relaxed and spent and fucking brilliant, and when he told Evelyn as much, the Serperior snickered, sounding just as exhausted as Marcus himself.

"Fuckin' love you," he said, pulling Evelyn into a hug.

**Notes for the Chapter:**

> Double-cocked snake Pokemon should be canon. For anyone wondering how Evelyn's Hemipenes looks like, feel free to google that term. Warning: Contains snake genitalia.  
> Tags are for the complete story - Marcus and Evelyn will explore what they can do together over the course of this work.
> 
> **You're welcome to leave prompts and suggestions in my Idea Collection. ☺**


	3. Chapter 3

There was an idea, or rather more a thought, niggling at the back of Marcus' mind. For weeks it was bothering the man now, especially when fooling around with Evelyn, his Serperior. He thought about it when he fucked him. He thought about it when sucking his cocks and playing with the silky smooth shafts and the awesome, red cockheads. He was thinking about it when trying out gay porn, watching dudes fuck each other silly. He was especially thinking about it when he was alone in his bad, writhing around with two fingers up his arse and crooked just right to hit his prostate, just as the articles he'd read suggested.

But it still took him weeks before he mentioned it to his only Pokemon in possession of cocks. They were lying on the bed, sheets crumpled and messy from the night before. It was early in the morning, and Marcus felt lazy and horny while stroking and softly tugging on Evelyn's hard cocks, brushing his hole ever so often to feel it twitch. There was still some dried cum coating the smooth rim - he'd later have to give Evelyn a thorough wash. "Hey, Evelyn," he asked, voice a bit morning rough, tilting his hips just right to rub his cock against Evelyn's scaly hide. The smooth, warm texture was nice. "Do you ever want to fuck me, too?"

He actually had to laugh when the Serperior perked up, blinking against the lingering sleepiness. He felt the cocks twitch against his hand, and with a grin, Marcus licked over his middle finger before pressing the tip into the smooth hole. Evelyn shuddered and coiled around him, nudging his shoulder with his head. "Is that a yes, then?", Marcus teased, causing Evelyn to hiss in annoyance. "Sheesh, I get it... Anyway, I was thinking about it. It's not like I'm not Bi, anyways, and I'm kinda curious how it feels like."

He got another hiss, longer and sharper, and Evelyn's long tongue darted out to give him a kiss. "Now is good, yeah. How about we start with that tongue thing you did last week? I definitely need some good preparation, bud, you're hung." He laughed again when Evelyn moved out like a Pokemon on a mission. His finger slipped out of the Serperior's hole as the elegant, heavy body slithered all across the Trainer until he could feel Evelyn nudge against his arse. "Gee, let me turn around first," Marcus complained, taking his time to roll onto his stomach and into a comfortable position. His hip got propped up by the Serperior, his legs slightly parted to make room for his own half-hard cock. "And don't rush it, you got that? Make me feel special." He chuckled at his own joke - more often than not he was rushing it himself, eager to wet his dick with Evelyn's tight hole. It had yet to go old, and despite the array of female Pokemon that were willing to let their Trainer mount them, he'd found himself preferring his very male Serperior as of late.

"Oh shit, yeah. That's the stuff," he grunted when Evelyn nosed between his arse cheeks, tongue darting out and over Marcus puckered hole. It had been weird as fuck the first time around, but since he'd started to finger himself, he'd noticed how sensitive that place was. His cock twitched pleasantly against warm, smooth scales and he closed his eyes, thoroughly enjoying the wet touch to his arse, especially when the tongue started to wiggle inside. There was a small stretch and burn, but light enough to actually feel pretty damn good. "That's a good boy, Evelyn... hmmm, yeah. Take your time with it, nice and slow."

If anyone ever was to give him shit for being eaten out by a Serperior, he'd laugh right into their faces. Marcus didn't give a fuck about public opinion. In fact, he bet that most Trainers had at least tried to fuck one of their Pokemon themselves. It was something very special indeed to tumble between the sheets with these powerful creatures, and Marcus wasn't ashamed of the fact that he got horribly turned on about that power difference. He was only a human, after all - Evelyn could kill him with one bite, but here he was, spread out on the bed with a Serperior pushing his tongue in his arse.

It didn't take long for them to go a step further - the wiggling tip of Evelyn's tail had given Marcus the idea, and when he started sucking on it, the Serperior had caught on quick fast. Which was how Marcus ended up worked open by slick-lubed, scaled tail, bearing against the burn until all was left was the pleasure of the tip rubbing against his prostate. "Fuck," he breathed, trying not to move lest Evelyn slipped out from it, eyes closed and breathing already ragged. His cock was fully hard now, the slit dripping precum from the jolts of hot pleasure that Evelyn made him feel. He heard him snicker at that and swatted at a coil of Evelyn's long body. "Yeah, yeah," he moaned, raising his hip a bit more. "Fuck me and all that, just... hnngh, this is fucking good, bud..."

No wonder Evelyn loved to get fucked by Marcus if this is how good it felt. It was just as good as fucking, but very different. It was still weird to feel himself loosen up as more of the tail slipped inside - he felt so full already, but he still wanted to experience that Serperior dick. "Evelyn, come on now," he grunted and pushed against the prodding tail. "Come on, I'm ready, please!"

It took him one minute of shifting positions and Evelyn lining up to regret the decision the moment the first wiggling cockhead breached his hole. It _burnt_ , but not in the good way. Not yet, anyway - from what he'd read, it would take some time for it to feel less like being ripped open and more like being fucked to the heavens, but right now Marcus had to bite back a curse, grinding his teeth and trying desperately to relax around the twitching thing between his cheeks. Evelyn noticed it, bless him, and went on even slower than before, coiling around to lick the now limp cock of his Trainer and nuzzling his balls. It helped a bit, but it took the two of them a few minutes of resting before Marcus was ready to go on. The cockhead slid fully into his arse, warm and foreign and not deep enough to reach his sweet point yet. Evelyn moved carefully, fucking him with just his tip, until the pain finally went away and his hole unclenched and opened up more.

This time they were prepared and took longer before Evelyn dared to add his second cockhead. Both grew out of his shaft at the very end, two dexterous and individually movable tips of one of his cocks - only after that the smooth, white shaft followed. It was painful yet again, but they both soldiered on, determined to make this happen. And when Evelyn was finally fully up his arse, those wonderfully textured heads carving out their space in his body, it felt really, really great. "Okay, I'm ready, you can move," Marcus said, the pain dimmed down to a throb now. His cock was still flaccid, but he felt new heat pooling in his stomach when Evelyn started to move forward. With a jolt, Marcus moaned - the Serperior had passed his prostate, and _fuck_ was that good.

The strong, muscular coils around his body tightened as Evelyn kept on moving, slowly upping the pace of his thrusts, angling them just right so that he hit Marcus' sweet spot more often than not. His second cock started to slap his balls and arse as the two rocked together, early difficulties forgotten as pleasure took over. Marcus wrapped both arms and legs around the tensing, scaled body of his lover, voice loud as he demanded more, harder, faster, oh please faster Evelyn - and his Serperior provided, slamming his midsection against Marcus' open arse, his cock pistoning in and out. Soon they started to writhe without any rhyme nor rhythm against each other, Marcus' cock wedged between their bodies, dripping precum and smearing it over those lovely green scales.

His orgasm came forcefully for Marcus, like a hit to his guts. His whole body tensed as he rutted against Evelyn, his arse clenching down on that lovely cock. Thick, creamy cum shot out of his throbbing cock and messed up his bed, and shortly after he was done, Evelyn followed suit. The Serperior squeezed the air out of his lungs, just for a moment before Evelyn gave a shudder and a hiss, his cocks pumping out that hot Serperior cum. Feeling it fill his arse up made Marcus growl in pleasure despite the exhaustion he felt.

"Fuck," he hissed, closing his eyes, his limbs going limp. He was still trying to catch up his breath and he felt his heartbeat slowing down a bit. "That was awesome, bud. Totally worth it." He stroke Evelyn's head, which rested on his chest, and leaned down to press a kiss onto his snout.

He was sure that with enough practise they could make it less painful as well.

**Notes for the Chapter:**

> Double-cocked snake Pokemon should be canon. For anyone wondering how Evelyn's Hemipenes looks like, feel free to google that term. Warning: Contains snake genitalia.  
> This is the last one - I wanted to do a fourth with Evelyn using both his cocks to fuck Marcus, but how would they even fit in there? So yeah, stopping it with Marcus finally knowing how a decent dicking feels.
> 
> **You're welcome to leave prompts and suggestions in my Idea Collection. ☺**


End file.
